Dimethyl Sulfide → HCID 131729193, compound

HRID 911833Notes

Reaction equation

S(C)C.[CH3:4][C:5]1[N:6]=[C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([S:17][CH:18]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[CH:13][C:12]=2[O:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[S:8][CH:9]=1.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[CH3:4][C:5]1[N:6]=[C:7]([NH:10][C:11]2[C:12]([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:13][C:14]([S:17][CH:18]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[CH:15][N:16]=2)[S:8][CH:9]=1

Participants

Reactant 3

HCID 1068Dimethyl Sulfide

HCID 6422Trifluoroacetic acid

HCID 86631500HCID 86631500, compound

Product 1

HCID 131729193HCID 131729193, compoundYield 90%

Procedure

Placed Me2S (0.0072 g, 0.12 mmol) in Trifluoroacetic acid (10 mL) followed by tert-butyl 4-((6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)(pyridin-2-yl)methyl)piperidine-1-carboxylate (0.068 g, 0.12 mmol) stirred at ambient temperature for 30 minutes, then concentrated to give the title compound (0.086 g, 90% yield). 1H NMR (d6-DMSO) δ 8.52 (bs, 1H), 8.42 (m, 1), 8.17 (bs, 1H), 8.00 (d, 1H), 7.70 (dt, 1H), 7.41 (t, 2H), 7.25-7.16 (m, 3H), 6.92 (d, 2H), 6.90 (s, 1H), 6.63 (s, 1H), 4.22 (d, 1H), 3.32 (d, 1H), 3.17 (d, 1H), 2.9872.74 (m, 2H), 2.30 (m, 2H), 2.23 (s, 3H), 1.45 (m, 2H), 1.30 (m, 1H).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-375377b86e754bdfa9c7baaf9ffed357
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022223B2

Reaction notes

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